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ChemInform Abstract: Synthetic Studies on Sphingolipids. Part 5. Stereocontrolled Synthesis of Novel Phytosphingosine-Type Glucosaminocerebrosides.

✍ Scribed by Teiichi Murakami; Kazuhiro Taguchi

Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthetic Studies on Sphingolipids. Part 5. Stereocontrolled Synthesis of Novel Phytosphingosine-Type Glucosaminocerebrosides.

-Phytosphingosine (X) is prepared by an improved route involving regioselective O-methanesulfonation and diastereoselective Grignard addition as key steps. The novel glucosamino-cerebrosides (XIV) are prepared from intermediate (VIII) as glycosyl acceptor and chloroacetamido derivative (XI) as efficient glucosamine donor. The route via dechlorination of the chloroacetamido group is proved to be more effective as the direct route via the N-acetyl analogue of (XI). The use of the N,O-oxazoline-protected sphingosine (VIII) has the advantage that various fatty acids can be installed onto the sphingosine amino group after glycosidation.

-(MURAKAMI, TEIICHI; TAGUCHI, KAZUHIRO;

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